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Synthesis method of O-(3-chloro-2-propenyl) hydroxylamine

A synthetic method and propylene-based technology, applied in the direction of hydroxylamine, chemical instruments and methods, nitrogen compounds, etc., can solve the problems of large amount of three wastes, low production efficiency, inconvenient industrialization, etc., to reduce salt content, improve product yield and quality, and the effect of reducing the cost of wastewater treatment

Pending Publication Date: 2021-05-28
SHANGHAI DONGGENG CHEM TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0015] In view of the above-mentioned shortcoming of the prior art, the object of the present invention is the synthetic method of O-(3-chloro-2-propenyl) hydroxylamine, for solving O-(3-chloro-2-propenyl) in the prior art ) Hydroxylamine has problems such as high synthetic cost, low production efficiency, high energy consumption, large amount of three wastes, and inconvenient industrialization.

Method used

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  • Synthesis method of O-(3-chloro-2-propenyl) hydroxylamine
  • Synthesis method of O-(3-chloro-2-propenyl) hydroxylamine
  • Synthesis method of O-(3-chloro-2-propenyl) hydroxylamine

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preparation example Construction

[0031] The invention provides a kind of synthetic method of O-(3-chloro-2-propenyl) hydroxylamine, comprises the steps:

[0032] (1) Treat an aqueous solution of hydroxylamine salt (hydroxylamine hydrochloride or hydroxylamine sulfate) with a basic ion exchange resin to obtain a hydroxylamine solution. The reaction formula is:

[0033]

[0034] (2) After preheating the hydroxylamine solution and methyl isobutyl ketone, pump them into the first-stage microchannel reactor respectively, and react to obtain methyl isobutyl ketone oxime, and then the reaction solution flowing out of the microchannel reactor directly enters the first-stage microchannel reactor. In the secondary microchannel reactor, continue to react with 1,3-dichloropropene and liquid caustic soda. After the reaction, the reaction solution is adjusted to weak acidity with acid, and the phases are separated. The aqueous phase is extracted with methyl isobutyl ketone and combined. The organic phase is washed with...

Embodiment 1

[0050] The synthetic method of O-(3-chloro-2-propenyl) hydroxylamine in the present embodiment comprises the steps:

[0051] Hydroxylamine hydrochloride (70.0g, 1mol) aqueous solution is passed through the 717 strong basic styrenic anion exchange resins that have been processed, and the effluent liquid is pumped in the first-stage microchannel reactor at room temperature, and simultaneously pumps into methyl isobutyl ketone ( 150g, 1.5mol), react, and the reaction temperature is controlled at 80-100 ℃; The effluent of the first stage microchannel reactor directly enters in the second stage microchannel reactor, and simultaneously adds 1,3-dichloropropene (116.6 g, 1.05mol), 30% sodium hydroxide (147g, 1.1mol) solution, continue the reaction, and the reaction temperature is controlled at 80-90°C; after the reaction, the phases are separated, and the aqueous phase is extracted with methyl isobutyl ketone (50mL × 3), the organic phase and the extraction phase were combined, washe...

Embodiment 2

[0054] The synthetic method of O-(3-chloro-2-propenyl) hydroxylamine in the present embodiment comprises the steps:

[0055] Hydroxylamine hydrochloride (70.0g, 1mol) aqueous solution is passed through the 717 strong basic styrenic anion exchange resins that have been processed, and the effluent liquid is pumped in the first-stage microchannel reactor at room temperature, and simultaneously pumps into methyl isobutyl ketone ( 150g, 1.5mol), react, and the reaction temperature is controlled at 20-50 ℃; The effluent of the first-stage microchannel reactor directly enters in the second-stage microchannel reactor, and simultaneously adds 1,3-dichloropropene (116.6 g, 1.05mol), 30% sodium hydroxide (147g, 1.1mol) solution, continue to react, the reaction temperature is controlled at 50-60 ℃; × 3), the organic phase and the extraction phase were combined, washed with water and then azeotropically dewatered, and the solvent was recovered to obtain 100.8 g of O-(3-chloro-2-propenyl) h...

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Abstract

The invention belongs to the technical field of organic synthesis, and particularly discloses a synthesis method of O-(3-chloro-2-propenyl) hydroxylamine. The synthesis method comprises the following steps of: carrying out a heating reaction on a hydroxylamine solution and methyl isobutyl ketone to obtain methyl isobutyl ketoxime, then carrying out a reaction on the methyl isobutyl ketoxime, 1, 3-dichloropropene and an alkali liquor, after the reaction is finished, adjusting the reaction liquid to be weakly acidic by using acid, carrying out phase splitting, extracting a water phase by using methyl isobutyl ketone, combining organic phases, washing with water, removing water, and recovering the methyl isobutyl ketone to obtain the product 0-(3-chloro-2-propenyl) hydroxylamine. According to the method, methyl isobutyl ketone serves as an amino protective agent and a solvent at the same time, the molecular structure is not changed before and after the reaction, the defects that a large amount of ethyl acetate is consumed and acetic acid and sodium chloride are produced as byproducts in a traditional process can be overcome, and the method is an efficient, environment-friendly and high-yield 0-(3-chloro-2-propenyl) hydroxylamine synthesis method and is suitable for industrial production.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a method for synthesizing a pesticide intermediate O-(3-chloro-2-propenyl)hydroxylamine. Background technique [0002] O-(3-chloro-2-propenyl)hydroxylamine (chlorinated amine) belongs to alkoxyamine compounds, which are widely used and expensive organic synthesis intermediates. Alkoxyamine compounds can be used as alkyl amination reagents, introducing alkoxyamine groups to ketone compounds (especially steroids) in organic synthesis and new drug production, and can be used as intermediates in drug production , can also be used as an intermediate in the field of synthesis of new medicines and new pesticides. O-(3-chloro-2-propenyl) hydroxylamine is an important intermediate of clethodim, and can also be widely used in the synthesis of other cyclohexenones Oxime herbicides, such as Tepraloxydim, Cycloxydim, Tralkoxydim, Butroxydim, Clefoxidim, etc. This type of herbicide...

Claims

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Application Information

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IPC IPC(8): C07C239/20C07C249/08C07C251/38C07C249/12C07C251/54C01B21/14
CPCC07C249/08C07C249/12C07C239/20C01B21/1409C07C251/38C07C251/54
Inventor 郑晨郑伯川邹志刚康小玲唐曦
Owner SHANGHAI DONGGENG CHEM TECH CO LTD
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